
The confrontation in “The Ask” involves no guns, nor even any shouting. It’s not a confrontation at all, by any typical definition these days in either theater or politics. Greta, a long-time donor to the American Civil Liberties Union, stopped contributing to the organization last year, and Tanner, a fundraiser for the ACLU, is paying a visit to Greta in her tasteful Upper West Side apartment to get her to resume. What unfolds over the eighty minutes of Matthew Freeman’s subtle, intelligent two-character play is not so much a clash of worldviews, but small, specific differences that provoke some large questions – about the complexity of power, and freedom, and change.
Betsy Aidem portrays Greta, a photographer and recent widow in her 70s who first heard of the ACLU in her twenties because of their principled stand on behalf of the First Amendment defending Nazis who wanted to march in the Jewish suburb of Skokie, Illinois. She was finally prompted to join as an act of defiance a decade later in 1988 when during a Presidential debate George H.W. Bush accused Michael Dukakis of being a card-carrying member of the ACLU.
“I don’t know if you remember, or no you weren’t even born yet.”
“I’ve heard about it,” Tanner replies. (What else can she say?)
Colleen Litchfield plays Tanner, a newly hired fundraiser in their twenties who was a theater major in college. Tanner is non-binary – goes by “they” – which is handled especially well. It’s never really spelled out – Tanner is guarded — but we understand it as underlying some of the personal tension that develops between the two, most notably when Tanner refers to “pregnant people,” rather than pregnant women. “I am not trying to be insensitive,” Greta reacts, “but you have to understand, I have fought for women’s rights my whole life.” Does Greta realize in her comment that she is being insensitive to Tanner, or is she speaking more generally? The ambiguity is instructive. It reflects their respective positions, not just in life, but in this conversation. Greta, the one with the money to give, can express herself and her opinions freely with no repercussions. Tanner, who has been hired to do the job of convincing donors to give their money, must be careful not to offend any of them. One of the exchanges that illustrates the power dynamic occurs when Tanner runs down various ways to structure charitable contributions that could yield tax savings; Greta expressions confusion; and Tanner attempts to clarify:
“The best gift for you is the gift I hope you’ll make. Whatever that means for you.”
“That doesn’t mean anything to me.”
Tanner handles this dance professionally, but there is a moment that reveals the stress it causes: When Greta goes into another room to take a phone call, Tanner breaks down crying.

We eventually learn that Greta paused her contributions to the ACLU because of the way she feels it has engaged in “mission creep” from its original laser focus on defending the Constitution to a “progressive wish-list,” such as fighting to eliminate student debt, much of which has nothing to do with the Constitution. She also objects to an attitude that Greta finds self-defeating: “Everything is systemic. It removes cause and effect on the personal level. It removes the individual.”
Tanner, who half-jokes that she’s happy about the ACLU position of student debt “as a person with student loans,” then gingerly makes a sophisticated case for the organization fighting for more equitable access in general, because “access impacts our rights. A right without access doesn’t really exist. “ A back-and-forth ensues that is fascinating, made all the more so because of the expressive interplay between these two pros — Aidem, who was Tony nominated for her role as the mother in Prayer for the French Republic, and Litchfield, who debuted on Broadway in “Leopoldstadt”
It might be easy for a theatergoer to conclude that the play is about a generational divide, and that it takes sides in that divide. This is, after all, a real-life debate within the ACLU, and progressive circles more generally, that has been doing on for years (“Once a Bastion of Free Speech, the A.C.L.U. Faces an Identity Crisis,” NY Times, 2021.) But part of the beauty of “The Ask” are the various ways the playwright resists such an easy summary. We see explicit – even parallel – sympathy for each side. Greta recounts how a salesman at a car dealership in Florida wouldn’t sell her a car without her husband present. Tanner recounts how someone in a Walmart in Texas followed Tanner into a bathroom accusing them of using the wrong one.
Freeman, who has worked for more than a dozen years as a fundraiser for the ACLU, keeps to the concrete and specific of how such a conversation would realistically play out. It’s up to each theatergoer individually to extrapolate the lessons. “The Ask” makes us confront our own assumptions, which is the best kind of confrontation that theater can create.
The Ask
Wild Project through September 28
Running time: 80 minutes no intermission
Tickets: $58.59
Written by Matthew Freeman
Directed by Jessi D. Hill
Scenic Design by Craig Napoliello
Lighting Design by Daisy Long
Sound Design by Cody Hom
Costume Design by Nicole Wee
Cast: Betsy Aidem as Greta and Colleen Litchfield as Tanner